CN106242990B - Preparation method of 2-amino-4-acetamino anisole - Google Patents
Preparation method of 2-amino-4-acetamino anisole Download PDFInfo
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- CN106242990B CN106242990B CN201610605385.3A CN201610605385A CN106242990B CN 106242990 B CN106242990 B CN 106242990B CN 201610605385 A CN201610605385 A CN 201610605385A CN 106242990 B CN106242990 B CN 106242990B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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Abstract
The invention relates to a preparation method of 2-amino-4-acetamino anisole, belonging to the technical field of hydrogenation reduction reaction of 2-nitro-4-acetamino anisole. In a reaction system with water as a solvent, 2-nitro-4-acetamino anisole is catalytically hydrogenated and reduced into 2-amino-4-acetamino anisole in the presence of an acid-binding agent and a catalyst, the catalyst is separated and recovered by solid-liquid separation, and the 2-amino-4-acetamino anisole is obtained by cooling and crystallization.
Description
Technical Field
The invention relates to a preparation method of 2-amino-4-acetamino anisole, belonging to the field of chemical industry.
Background
2-amino-4-acetamidoanisole
(CAS:6375-47-9, 2-Amino-4-acetylaminoanisole, molecular weight: 180.2)
The structural formula is as follows:
the 2-amino-4-acetamino anisole is an important intermediate for dye and medicine production, is mainly used as a disperse dye intermediate, is also used for synthesizing acid dye, reactive dye and pigment, and plays an important role in industry. Mainly used for dispersing blue 79#、291#And the like, and has a large market at home and abroad.
The prior hydrogenation reduction preparation method of 2-amino-4-acetamino anisole is a conventional organic solvent such as methanol catalytic hydrogenation method, and because the organic solvents such as methanol are flammable and explosive, the danger coefficient is higher under the condition of higher reaction pressure, and larger hidden danger exists in the aspect of safety; and a step of recycling methanol is needed, the energy consumption required by the step is huge, the distilled wastewater also needs to be further treated, and the product cost is increased.
Disclosure of Invention
The invention aims to provide a preparation method of 2-amino-4-acetamino anisole, which is environment-friendly, safe, economic and effective.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the invention provides a preparation method of 2-amino-4-acetamino anisole, which comprises a reaction step of generating the 2-amino-4-acetamino anisole from the 2-nitro-4-acetamino anisole, and is characterized in that water is used as a reaction solvent in the reaction step, and catalytic hydrogenation reduction reaction is carried out in the presence of an acid binding agent and a catalyst.
The method as described above, wherein the acid scavenger is selected from the group consisting of alkali metal salts, ammonia, NH4OH、KOH、Ca(OH)2、Na2CO3、NaHCO3One or more than two of sodium acetate; preferably, the acid scavenger is selected from NaOH, KOH, Ca (OH)2、NH4OH, sodium acetate, Na2CO3、NH4One or more than two of OH.
The dosage of the acid-binding agent can be 1 per thousand-10 percent of the mass of the reactant, and is preferably 4 per thousand-6 percent;
the process as described above, wherein said catalyst is selected from the group consisting of raney nickel metal catalyst, skeletal nickel metal catalyst, noble metal catalyst; preferably, the catalyst is selected from one or two of raney nickel and framework nickel.
The dosage of the catalyst can be 1 per mill to 20 percent of the mass of the reactant, and is preferably 1 percent to 6 percent;
as a specific embodiment of the present invention, the method is characterized in that:
(1) taking water as a solvent, taking 2-nitro-4-acetamino anisole as a raw material, adding the acid-binding agent, controlling the temperature at 50-180 ℃, and introducing hydrogen under the condition of the existence of the catalyst to perform catalytic hydrogenation reduction reaction for 0.1-24 h;
(2) after the reaction is finished, carrying out solid-liquid separation and recovering the catalyst;
(3) cooling and crystallizing to obtain the 2-amino-4-acetamino anisole product.
In the above process, the amount of the catalyst added may be, for example, 1% to 25% by mass of the raw material, and more preferably 8% to 10% by mass of the raw material.
Preferably, the catalytic hydrogenation reduction reaction time is 1-5h, the reaction temperature is 80-120 ℃, and the pressure is controlled to be 0.1-10 MPa.
More preferably, the catalytic hydrogenation reduction reaction time is 4-5h, the reaction temperature is 80-95 ℃, and the control pressure is 2.0-3.0 MPa.
Preferably, the method is a method in which the pH value of the reaction system in the catalytic hydrogenation reduction reaction is controlled to be 1 to 12, preferably 7.5 to 10.0, and more preferably 7.5.
In the method, as a specific embodiment, 2-nitro-4-acetamino anisole, water and Raney nickel are added into a closed reaction kettle, stirring is started, an acid binding agent is added, the temperature is increased to 80-95 ℃, when the system pressure is reduced to 2.0MPa, a hydrogen valve is opened, the hydrogen pressure is kept at 3.0MPa, the hydrogen valve is closed after the reaction is carried out for 4-5 hours under the pressure and temperature conditions, the pressure change in the kettle is observed, and if the pressure is reduced, the hydrogen is continuously introduced until the pressure is unchanged. And after the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst for reduction of the next batch, cooling and separating out the filtrate, and filtering to obtain a finished product of the 2-nitro-4-acetamino anisole.
The dosage of the Raney nickel used as the catalyst is more preferably 8-10% of the mass of the 2-nitro-4-acetamino anisole. The catalyst can be used repeatedly.
The reaction solvent is water, and preferably, the volume mass ratio of the water to the 2-nitro-4-acetamino anisole is 3mL/g-30mL/g, and more preferably 10 mL/g.
Compared with the existing process method adopting an organic solvent as a reaction solvent, the method has the advantages of simple process under the condition of keeping good product quality and yield, environmental protection, safety, environmental protection, energy conservation and emission reduction due to no use of the organic solvent. In particular, it is possible to use,
compared with the C.I. disperse blue 79 prepared from the 2-amino-4-acetamino anisole (B) produced by an organic solvent method, the C.I. disperse blue 79 prepared from the 2-amino-4-acetamino anisole (A) produced by the method has the advantages that the purity, the chromatic light, the intensity and the sand grinding high-temperature dispersibility are improved to a certain extent. See the following table for details:
purity was determined by liquid chromatography, which is commonly used in the art for determining the product. The high-temperature dispersion stability determination method is referred to the national standard GB/T5541-2007. The method for measuring the intensity and the color light is disclosed in the national standard GB/T10662-2007.
Detailed Description
The following examples are intended to illustrate or explain the invention without further limiting it.
Example 1
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding acid-binding agent liquid alkali (3%) to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.7g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.38%, the content of the 2-amino-4-acetamino anisole is 96.67%, and the product yield is 94.06%.
Example 2
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 600mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding acid-binding agent liquid alkali (3%) to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.3g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.24%, the content of the 2-amino-4-acetamino anisole is 96.73%, and the product yield is 93.22%.
Example 3
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding acid-binding agent soda ash to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.7g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.28%, the content of the 2-amino-4-acetamino anisole is 96.71%, and the product yield is 94.10%.
Example 4
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding acid-binding agent ammonia water to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.6g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.25%, the content of the 2-amino-4-acetamino anisole is 96.69%, and the product yield is 93.85%.
Example 5
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding sodium acetate as an acid binding agent to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.9g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.35%, the content of the 2-amino-4-acetamino anisole is 96.98%, and the product yield is 94.82%.
Example 6
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 3g of Raney nickel into a closed reaction kettle, stirring, adding sodium acetate as an acid binding agent to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, wherein 40.4g of light brown granular product is obtained, the purity of the 2-amino-4-acetamino anisole is 97.78%, the content of the 2-amino-4-acetamino anisole is 93.86%, and the product yield is 88.48%.
Example 7
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 6g of Raney nickel into a closed reaction kettle, stirring, adding sodium acetate as an acid binding agent to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.9g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.35%, the content of the 2-amino-4-acetamino anisole is 96.83%, and the product yield is 94.66%.
Example 8
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding sodium acetate as an acid binding agent to adjust the pH value to 7.5, heating to 120 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature conditions, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, wherein 40.8g of light brown granular product is obtained, the purity of the 2-amino-4-acetamino anisole is 99.07%, the content of the 2-amino-4-acetamino anisole is 96.29%, and the product yield is 91.67%.
Example 9
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding sodium acetate as an acid binding agent to adjust the pH value to 7.5, heating to 95 ℃, controlling the system pressure within 1.5MPa, opening a hydrogen valve, keeping the hydrogen pressure at 1.0MPa, reacting for 3-4 hours under the pressure and temperature conditions, closing the hydrogen valve, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, wherein 38.2g of light brown granular product is obtained, the purity of the 2-amino-4-acetamino anisole is 99.18%, the content of the 2-amino-4-acetamino anisole is 95.7%, and the product yield is 91.2%.
Example 10
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and 5g of Raney nickel into a closed reaction kettle, stirring, adding acid-binding agent sodium acetate to adjust the pH value to 7.5, heating to 95 ℃, keeping the system pressure at 3.5MPa, opening a hydrogen valve, keeping the hydrogen pressure at 3.5MPa, reacting for 3-4 hours under the pressure and temperature conditions, closing the hydrogen valve, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 42g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.25%, the content of the 2-amino-4-acetamino anisole is 96.71%, and the product yield is 94.78%.
Example 11
A method for preparing 2-amino-4-acetamino anisole by aqueous phase hydrogenation reduction of 2-nitro-4-acetamino anisole comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of water and a little fresh Raney nickel in example 1 into a closed reaction kettle, stirring, adding acid-binding agent sodium acetate to adjust the pH value to 7.5, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the pressure and temperature condition, observing the pressure change in the kettle, and if the pressure is reduced, continuously introducing hydrogen until the pressure is unchanged. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.5g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.19%, the content of the 2-amino-4-acetamino anisole is 96.65%, and the product yield is 93.59%.
Comparative example
A method for preparing 2-amino-4-acetamino anisole by reducing 2-nitro-4-acetamino anisole with methanol as solvent by hydrogen comprises the steps of adding 50g of 2-nitro-4-acetamino anisole, 500mL of methanol and 5g of Raney nickel into a closed reaction kettle, stirring, adjusting the pH value to 7.5 by using sodium acetate, heating to 95 ℃, opening a hydrogen valve when the system pressure is reduced to 2.0MPa, keeping the hydrogen pressure at 3.0MPa, closing the hydrogen valve after reacting for 3-4 hours under the conditions of the pressure and the temperature, observing the pressure change in the kettle, and continuously introducing hydrogen until the pressure is unchanged if the pressure is reduced. After the reaction is finished, stopping heating, filtering while the reaction is hot, separating and recovering the catalyst, cooling and separating out the filtrate, and filtering to obtain the 2-amino-4-acetamino anisole, thereby obtaining 41.1g of light brown granular product, wherein the purity of the 2-amino-4-acetamino anisole is 99.21%, the content of the 2-amino-4-acetamino anisole is 95.88%, and the product yield is 91.95%.
Claims (2)
1. A preparation method of 2-amino-4-acetamino anisole comprises a reaction step of generating 2-amino-4-acetamino anisole from 2-nitro-4-acetamino anisole, and is characterized in that water is used as a reaction solvent in the reaction step, a catalytic hydrogenation reduction reaction is carried out in the presence of an acid-binding agent and a catalyst, wherein the catalyst in the catalytic hydrogenation reduction reaction is Raney nickel, the addition amount of the catalyst is 8% -10% of the mass of the raw material, the acid-binding agent is added to adjust the pH value to 7.5-10.0, the reaction time is 4-5h, the reaction temperature is 80-95 ℃, and the control pressure is 2.0-3.0 MPa.
2. The method of claim 1, wherein saidThe acid-binding agent is selected from NaOH, KOH, Ca (OH)2、NH4OH, sodium acetate, Na2CO3And one or more than two of ammonia water.
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| CN106866449B (en) * | 2017-03-31 | 2018-01-05 | 九江善水科技股份有限公司 | A kind of method that the acetyl-anisidine of 2 amino 4 is prepared using 2,4 dinitrophenol hydrogenating reduction by-product recoveries |
| CN106966915B (en) * | 2017-04-21 | 2019-04-19 | 河南省科学院高新技术研究中心 | A kind of method of continuous production 2- amino -4- acetyl-anisidine |
| CN107746380B (en) * | 2017-11-06 | 2020-04-07 | 宁夏中盛新科技有限公司 | Industrial production method of 2-amino-4-acetamino anisole |
| CN116143649A (en) * | 2023-03-09 | 2023-05-23 | 宁夏中盛新科技有限公司 | Synthesis method of 2-amino-4-acetamido anisole |
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